Monoazo dyestuffs.



UNITED STATES PATENT OFFICE KARL HAGEMANN, OF LEVERKUSETI, NEAR COLOGNE. GERMANY, ASSIGNOR TO SYNTHETIC PATENTS CO., INC., OF NEW YORK, N. Y., A CORPORATION OF NEW' YORK MONOA ZO DYESTUFFS.

No Drawing.

To 117! 101mm 1/, may om-awn:

3e it known that I, KARL HAGEMANN, doctor of pliile.=.:o 'ihy, chemist, citizen of the icrnian linipire, residing at Lererkusen, near Cobgne-on-the-llhine, Germany, have imented new and useful Improvements in.

Monoaxo Uri-stalls. of which the following lf-I a apecilicatiml. 1

I ha\e l'eund that new and valuable azo (l\'e. can he obtained by combining the diazo r iupounda of ul'lllfltitlhld yl derivatives; of ortho-aniiur phcndl-sull'onic acids, such as paraauuin tcluolsulllenyl-Qamino-l- (or 0)" ehliirophenol-G- (or 4*) sull onic acid, metaaminobenzoylitaluino-l-chlorephenel-G-sull" nie acid, para-ainincbenzoyl-2-amino-G- ehloroplienel-4-sull'onic acid, 1neta-amin i benxoyl-2-ai'ninophenoll-sultenic acid, with on being al't -rir'cated \rith bichron e, the change being from an orange to the red or blueied side, according to the colorused. Contrahy to tin-M: rl ye. ,tulls, the new prodil 'i'-1 alter but very lil'tle'when after-treated i with biehroine. They give pure yellow shades diFtinguishi-d by great clean-nus 7 fastnes's to niillin; and excellent l'astneafto light The new fl wi'i are after being dr ed and pulwrizcd .in the nhape f th ir all-Ialini- :-alt:-- lilllliFlil)l'() '\li to' )lllo \'i$ll ponderr: :y-luldr in \\ater. caustic .-.oda lye and con ntrated sull'urii; aeiiL gi-i i' rallf; with a it-llorvish ceiozalioi'i. upon redu tion \il ith a tic aPi-l and zin powder an aminoa idyi CHIP "Hill ol an ortho-aminoph nol .-ull' -nic a id and a i aminepyra olou, compound ,Yellewireh to pure yell w r-l-rome lalres very last to light and last to milling can he produced on thejii'ievwith the ne vceloring matters. F

In order to illustrate Hm m process more Specification of Letters Patent.

Patented Feb. 2, 1915.

Application filed April 21, 1914. Serial No. 833,468

fully the following example is given, the parts being by weight: 39.2 parts of paraaminotoluol sulfcnyl ortho arnim phenol- 1iara-chloro-ortho-sulfcnic acid are di. lved in 1000 parts of water and PLU'tS of soda and diazotized with 42 parts of hydrochloric acid 11);? B. and 6.9 parts of sodium n'itrite The diazo compound thus obtained then stirred into a (old solutien oi ii'parts of l ortho chloro meta sulfophenyl 3 inetlurl-5-pyrazolon and a solution of 40 parts of s dium bicarbonate is added to obtain a weakly alkaline reaction. After qtii ring the ct 'nilation soon complete. and the dyeetull is salted ent and liltered'ofl'v It is after being dried and pulverized in the shape of its sodium salt a canary-yellow powder soluble in water and concentrated su'l'uric acid with a yellowish coloration and yielding; upon reduction with zinc powder I and m etic acid paraan'iino-toluelsullenyl-2- amino-4411ilero-l-phenral-6-sulfenie acid and 1- (Z chloro-ZB sull'ophenyl) 3 methyl 4- aniino-5-pyrazolon. It has in a free state lllCSt/ probahlythe formula:

oration; yielding upon reduction with acetic acid and zme powder an aminoacidyl are a iterheing dried and pulycrized waders soluble in liter. caustic soda lre and concentrated f stulfurie acid generally with a yellowish 0 01 compound 10f an ''fortho aminqphenol-sulcoloration;

-st ufi's being derived from fonic acid and a 4-aminopyrazolon compound furnishing on the fiber yellowish to pure yellow chrome lakes fast to light and to milling, substantially as described.

The herein described new azo dyestuffs being derived from an amino-arylacidylcompound of an ortho-amino-phenolsulfonic acid and a pyrazolone compound. which are after being dried and pulverized in the shape of their alkaline salts reddishbrown to yellowish powders soluble in water, caustic soda lye and Concentrated sulfuric acid generally with a yellowish colorationz'yielding upon reduction with acetic acid and zinc powder an amino-arylacidyl compound of an ortho-aminophenolsulfonic acid and a 4-aminopyrazolon compound furnishing on the fiber yellowish to pure yellow chrome lakes fast to light and to milling, substantially as described. Y

3. The herein described new azo dyestuffs being den-ed from an amino-arylsulfonyl compounl of an ortho-amino-phenol-sulfonic acid and a pyrazolone compound, which are after being dried and pule verized in the shape of their alkaline salts reddish-brown to yellowish powders soluble in water, caustic soda lye and concentrated sulfuric acid generally with a yellowish coloration; yielding upon reduction with acetic acid and zinc powder an amino-arylsulfonyl compound of an ortho-aminephenol-sulfonic acid and a l-aminopyrazolon' compound furnishing on the fiber yellowish to pure yellow chrome lakes fast to light and to milling, substantially asdescribed.

4. The herein described new azo dyestufl's being derived from an aminoacidyl nol-sulfonic acid and. a pyrazolone compound, which are after being dried and pulverized in the shapeof their alkaline salts reddish'brown to yellowish powders soluble in water, caustic soda lye and concentrated sulfuric acid generally with a yellowish w elding upon reduction with acetic acid and zinc powder an amino-acidyl compound of an ortho-amino-chloro-phenol-sulfonic acid and a 4-aminopyrazolon compound furnishing on the fiber yellowish to pure yellow chrome lakes fast to light and to milling. substantially as described 5. The herein described new azo dyean 'amino-arylacidyrl'comnound of an ortho-amino-chloroplien'ol-sulfonic acid and a pyrazolone com-' pound. which are after being dried and pulverized in-the shape of their alkaline salts f reddish-brown to yellowish powders soluble ace .in water, caustic soda lye and concentrated sulfuric acid generally with a yellowish I coloration: yielding upon reduction with acetic acid and zinc powder an amino-arylacidvl com ound of an ortho-amino-cblorophenol-sulfomc acid and a 4-aminopyrashape of their alkaline salts reddishbrown to yellowish powders soluble in water, caustic soda lye and concentrated sulfuric acid generally with a yellowish coloration;

yielding upon reduction with acetic acid and zinc powder an amino-acidyl compound are after being dried and pulverized in the of an ortho-aminophenol-sulfonic acid and a 4-amino-pyrazolon-sulfonic acid furnishing on the fiber yellowish to pure yellow chrome lakes fast to light and to milling, substantially as described.

7. The herein described new azo dyestuffs being derived from an aminoacidyl compound of an ortho-amino-phenol-sulfonic,

acid and a phenylmethylpyrazolon compound, which .are after bein dried and pulverized in the shape of their alkaline salts reddish-brown to yellowish powders soluble in water, caustic soda' lye and concentrated sulfuric acid generally with a yellowish coloration; yielding upon reduction with acetic acid and zinc powder an amino-acidyl compound of an ortho-aminophenol-sulfonic acid and a 4amino-phenylmethylpyrazolon compound furnishing on the fiber yellowish to pure yellow chrome lakes fast to light and to milling. substantially as described.

8. The herein described new azo dyestuffs being derived from an aminoacidyl compound of an ortho-aminophenol sulfonic acid and a chlorophenylmethylpyrazolon compound, which are after bein dried and pulverized in the shape of theira kaline salts reddish-brown to yellowish powders soluble being derived from an aminoacidyl compound of an ortho-aminophenol-sulfonic,

acid and a chlorophenylmethylpyrazolon sulfonic acid, which are after being dried and pulverized in the shape of their alkaline salts reddish-brown to yellowish powders solpble in water, caustic sodalye and concentrated sulfuric acid generally with a yellowish coloration: yielding upon reduction with acetic acid and zinc powder an amino-acidyl compound of an ortho-aminophenol-sultonic acid and a 4-amino-chlorophenylmethyl yrazolon sulfonic acid furnishing on the ti er yellowish to pure yellow chrome lakes fast to light and to milling, substantially as described.

10. The herein described new azo dyestufi's being derived from an amino-aryl-acidyl compound of an ortho-aminochloro-phenolsulfonic acid and a pyrazolon sulfomc acid which are after being dried and pulverized in the shape of theiralkaline salts reddishbrown to yellowish powders soluble in water, caustic soda lye and concentrated sulfuric acid generally with a yellowish coloration yielding upon reduction with acetic acid and zinc powder an amino-aryl-acidyl compound of an ortho-amino-chloro-phenol-sulfonic acid and a 4-amino-pyrazolon-sulfonic acid furnishing on *the fiber yellowish to pure yellow chrome lakes fast to light and to milling, substantially as describe 11. The herein described new azo dyestuffs being derivedfrom an amino-aryl-acidyl compound of an ortho-amino-chloro-phenolsulfonic acid aiid a chlorophenylmethylpyrazolon sulfonic acid, which are after being dried and pulverized in the shape of their alkaline salts reddish-brown to yellowish powders soluble in water, caustic soda lye and concentrated sulfuric acid generally with a yellowish coloration; yielding upon reduction with acetic acid and zinc powder an amino-aryl-acidyl compound of an orthoamino-chloro-phcnol-sulfonic acid and a 4- aminochlorophenylmethylpyrazolon sulfonic acid furnishing on the fiber yellowish to pure to mi 12. The herein described new azo having in a free state most probably the formula v on on.

A soul-E 1 -ua-so,-

0 a a --N C1 1 J L 4' a 2 l :(u \84 1N/ which is after being dried and pulverized in the shape of its sodium salt a canaryyellow powder soluble in water and concentrated sulfuric acid with. a yellowish coloration and yielding upon reduction with zinc powder and acetic acid para-amino-toluol-sulfonyl- Q-aminol-chloro-l-phenol 6 sulfonic acid and 1- (2'-chloro-5-sulfophenyl)-3-methyl- 4-amino-5-p razolon and furnishing when printed on t e fiber together with acetate of chromium pure yellow shades fast to li ht and to milling, substantially as describe I In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

KARL HAGEL'IANN.

Witnesses Cons VANDORY, Hans Platinum. 

